Question

Is 2-bromo-3-methylpentane a meso compound?

Answer 1

No, none of the optical isomers of 2-bromo-3-methylpentane is a meso compound.

The structure of 2-bromo-3-methylpentane is

CH₃CH₂-CH(CH₃)-CHBr-CH₃

There are chiral centres at C-2 and C-3.

The atoms directly attached to C-2 are Br, C, C, and H.

The atoms directly attached to C-3 are C, C, C, and H.

We can see at once that they are not the same set of atoms. There can be no plane of symmetry in the molecule.

So no isomer of 2-bromo-3-methylpentane can be a meso compound.